Hollow ZIF-67-derived Co@N-doped carbon nanotubes boosting the hydrogenation of phenolic compounds to alcohols

The selective hydrogenation of highly toxic phenolic compounds to generate alcohols with thermal stability,environmental friendliness,and non-toxicity is of great importance.Herein,a series of Co-based catalysts,named Co@NCNTs,were designed and constructed by direct pyrolysis of hollow ZIF-67(HZIF-67)under H_(2)/Ar atmosphere.The evolution of the catalyst surface from the shell layer assembled by ZIF-67-derived particles to the in situ-grown hollow nitrogen-doped carbon nanotubes(NCNTs)with certain length and density is achieved by adjusting the pyrolysis atmosphere and temperature.Due to the synergistic effects of in situ-formed hollow NCNTs,well-dispersed Co nanoparticles,and intact carbon matrix,the as-prepared Co@NCNTs-0.10-450 catalyst exhibits superior catalytic performance in the hydrogenation of phenolic compounds to alcohols.The turnover frequency value of Co@NCNTs-0.10-450is 3.52 h^(-1),5.9 times higher than that of Co@NCNTs-0.40-450 and 4.5 times higher than that of Co@NCNTs-0.10-550,exceeding most previously reported non-noble metal catalysts.Our findings provide new insights into the development of non-precious metal,efficient,and cost-effective metal-organic framework-derived catalysts for the hydrogenation of phenolic compounds to alcohols.

Screening for Antioxidant Phenolic Compounds from Polygonum capitatum

[Objectives]To discover antioxidant natural products from the famous Hmong medicinal plant Polygonum capitatum.[Methods]The antioxidant activities of the isolated components were evaluated by ABTS and DPPH assays.[Results]A total of 27 free phenolics were isolated form P.capitatum.Then the in vitro antioxidant potential of these components was evaluated according to the DPPH and ABTS radical scavenging assays.Among them,five compounds(13,14,17,23,and 25)showed most significant ABTS radical-scavenging activity(IC 50 values of 3.81-15.09μg/mL).And 12 components(1,2,6,7,9,12,13,14,16,17,23,and 25)showed notable radical scavenging activity against DPPH(inhibition rates>88%).[Conclusions]Most of the above bioactive compounds were reported for the first time.

Mechanism of action of Balanophora involucrata polyphenolic compounds in the treatment of myocardial injury based on network pharmacology and molecular docking techniques

The objective of this work was to investigate the mechanism of action of Balanophora involucrata polyphenolic compounds in the treatment of myocardial injury.In the present study,Balanophora involucrata was extracted by refluxing 75%of ethanol.The obtained extract was extracted with petroleum ether,ethyl acetate and n-butanol respectively.And the ethyl acetate layer was separated.The extract was prepared by silica gel column chromatography,sephadex LH-20 elution and thin layer chromatography.After that,the Swiss target prediction database was utilized to obtain the targets of Balanophora involucrata,and the Genecards,OMIM and TTD databases were used to predict and screen the targets of Balanophora involucrata for the treatment of myocardial injury.The active ingredient-target network was constructed using Cytoscape software,and the PPI network was mapped using String database and Cytoscape software.GO bioprocess enrichment analysis and KEGG pathway enrichment analysis were performed by Metascape software to predict the mechanism of action.Molecular docking was performed in Discovery Studio 2016 client software to verify the binding of Balanophora involucrata polyphenols to key targets.In this study,six polyphenolic compounds were isolated from Balanophora involucrata.By GO enrichment analysis,1614 biological processes(BP),127 cellular compositions(CC),and 215 molecular functions(MF)were obtained;a total of 155 cross-targets were involved in the KEGG enrichment analysis.The PPI network showed that quercetin was the main active component of polyphenolic compounds against myocardial injury and that AKT1,EGFR,STAT3,SRC,ESR1,MMP9,HSP90AA1 and other related signals were associated with myocardial injury treatment.Finally,the multi-component-multi-target-multi-pathway action of Balanophora involucrata was concluded,which provided new ideas and methods for further research on the mechanism of action of Balanophora involucrata in myocardial injury.

Effect of pressure cooking on phenolic compounds of quinoa

Due to good nutritional properties and potential health benefits,quinoa has gained an increasing attention.The study aimed to analyze the effect of pressure cooking on the composition,antioxidant activity,antibacterial activity and bioavailability of phenolic compounds in four types of quinoa,and to evaluate the correlation between phenolics and its biological activities by correlation analysis.The results showed that different varieties of quinoa contained different phenolic components and their biological activities were different.Pressure cooking could significantly increase(P<0.05)the phenolic contents of quinoa,and decrease in vitro digestibility of protein.The antioxidant activity,antibacterial activity and bioavailability of quinoa were also enhanced which were positively related with phenolic contents.HPLC analysis indicated that at least twelve phenolic compounds were found in quinoa,and hyperoside,sinapic acid,rutin and ferulic acid occupied a majority of them.Correlation analysis suggested that hyperoside,quercetin,sinapic acid,ferulic acid and gallic acid made the key contribution to antioxidant and antibacterial activities of phenolic compounds of quinoa.The results provided valuable information for quinoa processing with phenolics as functional ingredient.

Effective anti-inflammatory phenolic compounds from dandelion:identification and mechanistic insights using UHPLC-ESI-MS/MS,fluorescence quenching and anisotropy,molecular docking and dynamics simulation

This novel study identifi es the effective anti-inflammatory phenolic compounds in dandelion and provides mechanistic insights into their interactions with receptor proteins(toll-like receptor 4,TLR4;co-receptor myeloid differentiation protein-2,MD-2)using UHPLC-ESI-MS/MS,lipopolysaccharide(LPS)-stimulated THP-1 cell line,fluorescence quenching and anisotropy,molecular docking(single ligand and multi-ligand docking)and molecular dynamics simulation.A 50%aqueous methanol extract had a greater anti-inflammatory effect and higher chicoric acid content,compared with the 100%water and 100%methanol extracts.Chicoric acid,chlorogenic acid,methylophiopogonone A,caffeic acid,gallic acid monohydrate and 4’-O-demethylbroussonin A had relatively high binding energies and contents in all extracts.Chicoric acid competed with chlorogenic acid,4’-O-demethylbroussonin A and quercetin for MD-2.Among dandelion’s phenolics,chicoric acid most effectively hindered TLR4-MD-2 complex formation,with a quenching constant of 0.62×10^(6) L/mol for MD-2 or TLR4 at 320 K,and binding energies of-6.87 and-5.97 kcal/mol,respectively,for MD-2 and TLR4.

Dual Role of Plant Phenolic Compounds as Antioxidants and Prooxidants

Natural phenolic compounds are secondary metabolites found in a wide range of plants including food crops. As many of them are known to be antioxidants and can prevent several chronic and degenerative diseases in humans, they are a part of a healthy diet. However, these antioxidants can act as prooxidants under high phenolic concentration, high pH, or in the presence of transition metal ions such as Cu2+ or Fe3+, producing reactive oxygen species (ROS) including hydroxyl radicals resulting in oxidative stress and cell toxicity. While this can lead to pathogenesis including the development of various types of cancers, elevated levels of ROS are beneficial to kill malignant cells and foodborne pathogens to improve food safety. Thus, the dual nature of phenolic compounds allows them to act as antioxidants and prooxidants. Similarly, depending on the level of prooxidant activity, ROS can induce either pathogenesis or serve as a potential agent to kill malignant cells and foodborne pathogens.

In Vitro and in Silico Insights on the Biological Activities, Phenolic Compounds Composition of Hypericum perforatum L. Hairy Root Cultures

Three Hypericum perforatum hairy root lines(HR B,HR F and HR H)along with non-transformed roots were analyzed for phenolic compounds composition and in vitro enzyme inhibitory properties.In silico molecular modeling was performed to predict the interactions of the most representative phenolic compounds in HR clones with enzymes related to depression,neurodegeneration and diabetes.Chromatographic analyses revealed that HR clones represent an efficient source of quinic acid and hydroxybenzoic acids,epicatechin and procyanidin derivatives,quercetin and kaempferol glycosides,as well numerous xanthones.In vitro antidepressant activity of HR extracts through monoamine oxidase A(MAO-A)inhibition was attributed to the production of oxygenated and prenylated xanthones.The neuroprotective potential of HR extracts was related to the accumulation of quercetin 6-C-glucoside,epicatechin,procyanidins andγ-mangostin isomers as potential inhibitors of acetylcholinesterase(AChE)and butyrylcholinesterase(BChE).Vanillic acid and prenylated xanthones in HR clones as promising inhibitors of tyrosinase additionally contributed to the neuroprotective activity.Five preeminent xanthones in HR(γ-mangostin,mangiferin,garcinone C,garcinone E and 1,3,7-trihydroxy-6-metoxy-8-prenyl xanthone)along with the flavonol quercetin 6-C-glucoside effectively inhibitedα-amylase andα-glucosidase indicating the antidiabetic properties of HR extracts.Transgenic roots of H.perforatum can be exploited for the preparation of novel phytoproducts with multi-biological activities.

Effects of different thermal processing methods on bioactive components,phenolic compounds,and antioxidant activities of Qingke(highland hull-less barley)

Qingke(highland hull-less barley)is a grain replete with substantial nutrients and bioactive ingredients.In this study,we evaluated the effects of boiling(BO),steaming(ST),microwave baking(MB),far-infrared baking(FB),steam explosion(SE),and deep frying(DF)on bioactive components,phenolic compounds,and antioxidant activities of Qingke compared with the effects of traditional roast(TR).Results showed that the soluble dietary fiber,beta-glucan and water-extractable pentosans of Qingke in dry heat processes of TR,SE,MB and FB had a higher content compared with other thermal methods and had a better antioxidant activity of hydroxyl radical scavenging and a better reduction capacity,while those in wet heat processes of BO and ST had a better antioxidant activity of ABTS radical scavenging and a better Fe^(2+) chelating ability.DF-and SE-Qingke had a higher content of tocopherol,phenolic,and flavonoid.Overall,6 free phenolic compounds and 12 bound phenolic compounds of Qingke were identified,and free phenolic compounds suffered more damage during thermal processing.Principal component analysis showed that SE had more advantages in retaining and improving the main biological active ingredients of Qingke,and it may be the best method for treating Qingke.

Study on Optimization of Ethanol Reflux Extraction of Phenolic Acids from Salvia miltiorrhiza

The extraction technology of phenolic acid compounds from Salvia miltiorrhiza by ethanol reflux was studied. In this experiment, salvianolic acid B standard was used to make the standard curve. Single factor experiment and orthogonal experiment were used to study the extraction of different ethanol concentrations, reflux times and material-to-liquid ratios. The OD value of salvianolic acid compounds was measured with a spectrophotometer. The extraction rate of phenolic acid compounds under different extraction conditions was calculated through a regression equation, so as to obtain the optimal conditions for the ethanol reflux extraction process of Salvia miltiorrhiza. The experimental data can provide a reference for the ethanol reflux extraction process of salvianolic acids in the industry. According to the experiment, the extraction rate of phenolic acids in Salvia miltiorrhiza was the highest when the ethanol concentration was 60%, the reflux time was 1.5 hours, and the ratio of material-to-liquid was 1:10.

Effect of Postharvest UV-C Irradiation on Phenolic Compound Content and Antioxidant Activity of Tomato Fruit During Storage

Mature-green tomato fruit （Solanum lycopersicum cv. Zhenfen 202） were exposed to different UV-C irradiation at 2, 4, 8, and 16 kJ m-2 and then stored under the dark at 14°C and 95% relative humidity （RH） for 35 d. Of these four doses, UV-C irradiation at 4 and 8 kJ m-2 significantly increased total phenolic contents in present tomato fruit by 21.2 and 20.2%, respectively. Furthermore, UV-C irradiation at 4 or 8 kJ m-2 promoted the accumulation of total flavonoids and increased the antioxidant activity. 2 or 16 kJ m-2 UV-C irradiation also enhanced antioxidant activity, but to a lesser extent. Seven phenolic compounds, viz., gallic acid, （＋）-catechin, chlorogenic acid, cafferic acid, syringic acid, p-coumaric acid, and quercetin in tomato fruit were identified and quantified by HPLC. Gallic acid was the major phenolic compound in tomato fruit and significantly correlated with antioxidant activity. 4 or 8 kJ m-2 UV-C irradiation significantly increased the contents of gallic acid, chlorogenic acid, syringic acid, p-coumaric acid, and quercetin. The optimum dose of UV-C irradiation in terms of increased phenolic compound content and enhanced Antioxidant activity was determined to be 4 or 8 kJ m-2.

Adsorption of phenolic compounds from aqueous solutions by aminated hypercrosslinked polymers

Two novel polymers （NJ-1 and N J-2） were synthesized by chemically modified a hypercrosslinked polymer NJ-0 with dimethylamine and trimethylamine, respectively. The comparison of the adsorption properties of the three polymers toward phenol, resorcin and phloroglucin was made. The study focused on the static equilibrium adsorption behaviors and the adsorption thermodynamics. Freundlich equation was found to fit the adsorption results well. The effect of amino groups introduced onto the surface of the resin and the structure of phenolic compounds on the adsorption were also studied. The hydrogen-bonding interaction and electrostatic interaction could happen between the amino groups and the adsorbates. The adsorption impetus increased as quantity of hydroxyl groups increased, but the adsorption capacity decreased due to the drop of the matching degree of the aperture of resins and the diameter of adsorbate molecules.

Phenolic compounds affect production of pyocyanin, swarming motility and biofilm formation of Pseudomonas aeruginosa

Objective: To investigate the effects of plant-derived phenolic compounds(i.e. caffeic acid, cinnamic acid, ferulic acid and vanillic acid) on the production of quorum sensing regulated virulence factors such as pyocyanin, biofilm formation and swarming motility of Pseudomonas aeruginosa(P. aeruginosa) isolates.Methods: Fourteen clinical P. aeruginosa isolates obtained from urine samples and P. aeruginosa PA01 strain were included in the study. The antibacterial effects of phenolic compounds were screened by well diffusion assay. Pyocyanin and biofilm activity were measured from culture supernatants and the absorbance values were measured using a spectrophotometer. Swarming plates supplemented with phenolic acids were point inoculated with P. aeruginosa strains and the ability to swarm was determined by measuring the distance of swarming from the central inoculation site.Results: Tested phenolic compounds reduced the production of pyocyanin and biofilm formation without affecting growth compared to untreated cultures. Moreover, these compounds blocked about 50% of biofilm production and swarming motility in P. aeruginosa isolates.Conclusions: We may suggest that if swarming and consecutive biofilm formation could be inhibited by the natural products as shown in our study, the bacteria could not attach to the surfaces and produce chronic infections. Antimicrobials and natural products could be combined and the dosage of antimicrobials could be reduced to overcome antimicrobial resistance and drug side effects.

Thermodynamic study of adsorption of phenolic compounds onto Amberlite XAD-4 polymeric adsorbents and its acetylized derivative MX-4

Adsorption equilibrium isotherms of phenolic compounds, phenol, p cresol, p chlorophenol and p nitrophenol, from aqueous solutions by Amberlite XAD 4 polymeric adsorbent and its acetylized derivative MX 4 within temperature range of 283 323K were obtained and fitted to the Freundlich isotherms. The capacities of equilibrium adsorption for all four phenolic compounds from their aqueous solutions increased around 20% on the acetylized resin, which may be contributed to the specific surface area and the partial polarity on the network. Estimations of the isosteric enthalpy, free energy, and entropy for the adsorption process were reported.

Phenolic compounds and its antioxidant activities in ethanolic extracts from seven cultivars of Chinese jujube

Phenolic compounds and its antioxidant activity of extracts from seven cultivars of Chinese jujubes were investigated by high performance liquid chromatography(HPLC)with standards and different antioxidant evaluation methods,such as phosphomolybdenum assay,superoxide radical scavenging activity(SRSA),hydroxyl radical scavenging activity(HRSA),antihemolytic activity and inhibition of lipid peroxidation in rat liver homogenate,respectively.The results showed the components of the extracts are comprised of total phenols and flavonoids,and its content ranges from 454.3 to 1298.9(GAE mg/100 g dry weight).Phlorizin,catechin,gallic acid,chlorogenic acid,caffeic acid were the predominant phenolic compounds.All the extracts had significant antioxidant activities either in vitro or in vivo.Correlation analysis indicated that the antioxidant capacities of Chinese jujube extracts demonstrated a good positive relationship with some phenolic acids,which was higher in Xiao and Goutou.The results indicated that Xiao and Goutou could be attributed to a potential source of natural antioxidants for food applications.

Phenolic compounds as natural feed additives in poultry and swine diets:a review

Due to ban on using antibiotics in feed industry,awareness of using natural feed additives have led to a great demand.The interest of plants phenolic compounds as a potential natural antioxidant source has been considered in research community due to their predictable potential role as feed additives in poultry and swine production.However,the mode of action for their functional role and dosage recommendation in animal diets are still remain indistinct.Taking into account,the present review study highlights an outline about the mode of action of phenolic compound and their experimental uses in poultry and swine focusing on the growth performance,antioxidant function,immune function,antimicrobial role and overall health status,justified with the past findings till to date.Finally,the present review study concluded that supplementation of phenolic compounds as natural feed additives may have a role on the antioxidant,immunity,antimicrobial and overall production performance in poultry and swine.

ADSORPTION BEHAVIOR OF PHENOLIC COMPOUNDS ONTO POLYMERIC ADSORBENTS MODIFIED WITH 2-CARBOXYBENZOYL GROUPS

Two hypercrosslinked polymeric adsorbents （ZH-01 and Amberlite XAD-4 resin） were employed to remove three kinds of phenolic compounds including phenol, 4-nitrophenol and 2,4-dinitrophenol from aqueous solutions. The study was focused on the static equilibrium adsorption behavior, the column dynamic adsorption and desorption profiles. The Freundlich model gave a perfect fitting to the isotherm data. The adsorbing capacities for these three compounds on ZH-01 were higher than those on Amberlite XAD-4 within the temperature range 288-318 K, which was attributed to the large micropore area and 2-carboxybenzoyl functional groups on the network of ZH-01 resin. The adsorption for phenol and 4- nitrophenol on ZH-01 was a physical adsorption process, while for 2,4-dinitrophenol it was a coexistence process of physical adsorption and chemisorption＇s transitions. The column test showed the advantages of ZH-01 in the dynamic adsorption processes of phenolic compounds. Being used as the desorption reagent, sodium hydroxide solution showed an excellent performance.

Changes of microbial community structures and functional genes during biodegradation of phenolic compounds under high salt condition

The changes of microbial community structures and functional genes during the biodegradation of single phenol and phenol plus p-cresol under high salt condition were explored.It was found that the phenol-fed system（PFS） exhibited stronger degrading abilities and more stable biomass than that of the phenol plus p-cresol-fed system（PCFS）.The microbial community structures were revealed by a modern DNA fingerprint technique,ribosomal intergenic spacer analysis（RISA）.The results indicated that the microbial community of PFS changed obviously when gradually increased phenol concentration,while PCFS showed a little change.16S rRNA sequence analysis of the major bands showed that Alcanivorax sp.genus was predominant species during phenolic compounds degradation.Furthermore,amplified functional DNA restriction analysis（AFDRA） on phenol hydroxylase genes showed that the fingerprints were substantially different in the two systems,and the fingerprints were not the same during the different operational periods.

Enhanced photodegradation of phenolic compounds by adding TiO_2 to soil in a rotary reactor

Photodegradation ofpentachlorophenol （PCP） and p-nitrophenol （PNP） in soil was carried out in a designed rotary reactor, which can provide the soil particles with continually uniform irradiation, and on a series of thin soil layers. TiO2, as a kind of environmental friendly photocatalyst, was introduced to the soil to enhance the processes. Compared with that on the soil layers, photodegradation of PCP at initial concentration of 60 mg/kg was improved dramatically in the rotary reactor no matter whether TiO2 was added, with an increase of 3.0 times in the apparent first-order rate constants. The addition of 1 wt% TiO2 furthered the improvement by 1.4 times. Without addition of TiO2, PNP （initial concentration of 60 mg/kg） photodegradation rate in the rotary reactor was similar to that on the soil layers. When 1 wt% additional TiO2 was added, PNP photodegradation was enhanced obviously, and the enhancement in the rotary reactor was 2 times of that on the soil layers, which may be attributed to the higher frequency of the contact between PNP on soil particles and the photocatalyst. The effect of soil pH and initial concentrations of the target compounds on the photodegradation in the rotary reactor was investigated. The order of the degradation rate at different soil pH was relative to the aggregation of soil particles during mixing in the rotary reactor. Photodegradation of PCP and PNP at different initial concentrations showed that addition of TiO2 to enhance the photodegradation was more suitable for contaminated soil with higher concentration of PCP, while was effective for contaminated soil at each PNP concentration tested in our study.

Multiple Response Optimization of High Temperature, Low Time Aqueous Extraction Process of Phenolic Compounds from Grape Byproducts

In this study phenolic compounds extraction from grape byproducts was conducted using pure water as a solvent. High temperatures and low time incubation periods were used in the aim of reducing the cost of the process and heightening the phenolic compounds yield. Response surface methodology (RSM) was realized to study the effect of time and temperature on crushed and uncrushed grape pomace. The phenolic content was evaluated considering the quantity (total phenolics (TPC), flavonoids (FC), total monomeric anthocyanins (TMA) and tannins (TC)), and quality (antiradical activity (AA) and antioxidant capacity (AC)) of the extracts. High temperature low time extraction design used in this study was compared to the extraction process at moderate temperatures with relatively long periods of time. This was proved to ameliorate the quantitative extraction of phenolic compounds from grape pomace without affecting their bioactivity. Moreover, multiple response optimization showed the optimal extraction parameters to be 81?C and 140 minutes for the unmilled pomace samples, and 88?C and 5 minutes for the milled. TPC, FC, TMA, TC, AA and AC are almost the same for both optimums. Thus the possibility of replacing the milling process by the extraction time prolongation (for the unmilled pomace) of 135 minutes seems to be very plausible. HPLC analysis showed different quantity and diversity of extracted phenolics for the optimums. However this difference did not significantly affect the overall activity, showing that PC in the different extracts act in complete synergy all together leading to important biological properties. The obtained results using the extraction strategy adopted in this work could lead to several industrial applications.

Extraction of Total Phenolic Compounds, Flavonoids, Anthocyanins and Tannins from Grape Byproducts by Response Surface Methodology. Influence of Solid-Liquid Ratio, Particle Size, Time, Temperature and Solvent Mixtures on the Optimization Process

The current work concerns the optimization process of phenolic compounds solid liquid extraction from grape byproducts at high temperatures and short incubation times. The effect of five experimental parameters (solidliquid ratio, particle size, time, temperature and solvent mixture) mostly believed to affect the extraction process was undertaken. A first response surface methodology experimental design was used to optimize the solid-liquid ratio and milling time parameters. A second design was used for the optimization of the quantitative and qualitative parameters. The quantitative parameters studied are: total phenolic compounds, flavonoid content, total monomeric anthocyanin composition and tannin concentration. The qualitative parameters analyzed are: antiradical activity and antioxidant capacity. The second design was based on the use of time, temperature and solvent mixture as optimization parameters. The assays were first conducted separately revealing the best experimental conditions for the maximization of each response variable alone. A simultaneous response surface methodology of all the responses taken together was then conducted, showing the optimal extraction conditions to be: 93 minutes at 94?C and in 66% ethanol/water solvent. The maximal response values obtained for each parameter are: Total Phenolic Compounds yield (5.5 g GAE/100g DM), Flavonoid Content (5.4 g GAE/100g DM), Total Monomeric Anthocyanin yield (70.3 mg/100g DM), Tannin Concentration (12.3 g/L), Antiradical Activity (67.3%) and Total Antioxidant Capacity (393 mgAAE/L). All of the optimal values were acquired at 3 mL/g solid-liquid ratio and 6.8 min milling time. The obtained extracts could be used as natural bioactive compounds in several industrial applications.